methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

Base Information

Chemical Name:methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate
CAS No.:404369-21-7
Molecular Formula:C₃₁H₃₇NO₃Si
Molecular Weight:499.725
Hs Code.:

Synonyms:methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

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Chemical Property of methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

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Technology Process of methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

There total 6 articles about methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 404369-20-6
methyl (2S,3S)-3-hydroxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

: 404369-21-7
methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(01)01070-5

Reference yield:

: 154494-79-8
methyl 2-deoxy-3,4-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-mannonate

: 404369-21-7
methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

Guidance literature:: Multi-step reaction with 6 steps

1: NaIO₄ / ethanol; H₂O / 3 h / 20 °C

2: 5.52 g / NaNH₄ / ethanol; H₂O / 0.17 h / 0 °C

3: 98 percent / Et₃N / tetrahydrofuran / 0.33 h / 20 °C

4: 95 percent / LiI / dimethylformamide / 80 °C

5: 85 percent / n-BuLi / tetrahydrofuran / 0.33 h / -40 °C

6: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; sodium periodate; n-butyllithium; triethylamine; lithium iodide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01070-5

Reference yield:

: (S)-((4R,5S)-5-Formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-(9-phenyl-9H-fluoren-9-ylamino)-acetic acid methyl ester

: 404369-21-7
methyl (2S,3S)-3-(tert-butyldimethylsilyl)oxy-2-[(9-phenyl-9-fluorenyl)-amino]-4-pentenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 5.52 g / NaNH₄ / ethanol; H₂O / 0.17 h / 0 °C

2: 98 percent / Et₃N / tetrahydrofuran / 0.33 h / 20 °C

3: 95 percent / LiI / dimethylformamide / 80 °C

4: 85 percent / n-BuLi / tetrahydrofuran / 0.33 h / -40 °C

5: 98 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; n-butyllithium; triethylamine; lithium iodide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)01070-5